JP6454252B2 - Black compound and method for producing the same - Google Patents
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- JP6454252B2 JP6454252B2 JP2015201808A JP2015201808A JP6454252B2 JP 6454252 B2 JP6454252 B2 JP 6454252B2 JP 2015201808 A JP2015201808 A JP 2015201808A JP 2015201808 A JP2015201808 A JP 2015201808A JP 6454252 B2 JP6454252 B2 JP 6454252B2
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Description
本発明は、黒色化合物及びその製造方法、並びにこの黒色化合物を用いた着色剤に関する。 The present invention relates to a black compound, a method for producing the same, and a colorant using the black compound.
アントラキノン系の色素は、キノイド系色素群のなかでも特に重要視されている。特に、１−アミノアントラキノンは多くの染料・顔料の基本骨格として知られており、これまでに多くの誘導体が合成されている。 Anthraquinone dyes are regarded as particularly important in the quinoid dye group. In particular, 1-aminoanthraquinone is known as a basic skeleton of many dyes and pigments, and many derivatives have been synthesized so far.
アミノアントラキノンを基本骨格とする顔料としては、例えば、Ｐｉｇｍｅｎｔ Ｒｅｄ １７７などがある。Ｐｉｇｍｅｎｔ Ｒｅｄ １７７は、１−アミノアントラキノンを二量化することによって製造される顔料である。また、アミノアントラキノンを基本骨格とする染料としては、例えば、Ａｃｉｄ Ｒｅｄ ８０などのアントラピリドン染料がある。このようなアントラピリドン染料は、１−アミノアントラキノンの環化反応により合成される（特許文献１）。 Examples of the pigment having aminoanthraquinone as a basic skeleton include Pigment Red 177. Pigment Red 177 is a pigment produced by dimerizing 1-aminoanthraquinone. Examples of the dye having aminoanthraquinone as a basic skeleton include an anthrapyridone dye such as Acid Red 80. Such an anthrapyridone dye is synthesized by a cyclization reaction of 1-aminoanthraquinone (Patent Document 1).
一方、アミノアントラキノンを基本骨格とする顔料のうち、黒色を呈するものとしては、例えば、１−アミノアントラキノンをジアゾ化する工程を含む合成方法によって製造される暗色系のアゾ顔料が提案されている（特許文献２）。 On the other hand, among pigments having aminoanthraquinone as a basic skeleton, dark azo pigments produced by, for example, a synthesis method including a step of diazotizing 1-aminoanthraquinone have been proposed. Patent Document 2).
しかしながら、特許文献２で提案されたアゾ顔料は、無彩色度及び黒色度が低いものであった。このため、他の色材と組み合わせて用いる等の調色を行う必要があった。 However, the azo pigment proposed in Patent Document 2 has low achromaticity and blackness. For this reason, it is necessary to perform toning such as using in combination with other color materials.
本発明は、このような従来技術の有する問題点に鑑みてなされたものであり、その課題とするところは、他の色材等と併用せずとも単独で黒色を呈することが可能な、無彩色度、黒色度、着色力、及び耐熱性に優れた黒色化合物を提供することにある。また、本発明の課題とするところは、上記黒色化合物の製造方法、及び上記黒色化合物を用いた着色剤を提供することにある。 The present invention has been made in view of such problems of the prior art, and the object of the present invention is that it can exhibit black alone without being used in combination with other coloring materials. The object is to provide a black compound having excellent chromaticity, blackness, coloring power, and heat resistance. Moreover, the place made into the subject of this invention is providing the manufacturing method of the said black compound, and the coloring agent using the said black compound.
すなわち、本発明によれば、以下に示す黒色化合物が提供される。
［１］下記一般式（１）で表される黒色化合物。
Ｘ−（Ｙ）n−Ｚ ・・・（１）
（前記一般式（１）中、Ｘ、Ｙ、及びＺは、下記一般式（Ｘ）、（Ｙ）、及び（Ｚ）で表される部分構造Ｘ、Ｙ、及びＺをそれぞれ示し、ｎは、１を示す）
That is, according to the present invention, the following black compound is provided.
[1] A black compound represented by the following general formula (1).
X- (Y) n -Z (1)
(In the general formula (1), X, Y, and Z represent partial structures X, Y, and Z represented by the following general formulas (X), (Y), and (Z), respectively, and n is , Indicating 1 )
前記一般式（Ｘ）中の＊ｘ1は前記一般式（Ｙ）中の＊ｙ11 に結合し、＊ｘ2は＊ｙ2に結合している。また、前記一般式（Ｙ）中の＊ｙ1は前記一般式（Ｚ）中の＊ｚ11 に結合し、＊ｙ22は＊ｚ2に結合している）
Before SL * x 1 in the general formula (X) is bonded to * y 1 1 in the general formula (Y), * x 2 is attached to the * y 2. Also, * y 1 in the general formula (Y) is coupled to * z 1 1 in the general formula (Z), * y 22 is that bonded to * z 2)
［２］前記一般式（Ｘ）、（Ｙ）、及び（Ｚ）中、Ｒ1が水素原子である前記［１］に記載の黒色化合物。 [2] The black compound according to [1], wherein R 1 is a hydrogen atom in the general formulas (X), (Y), and (Z) .
また、本発明によれば、以下に示す黒色化合物の製造方法が提供される。
［３］前記［１］又は［２］に記載の黒色化合物の製造方法であって、下記一般式（２）で表される化合物を１４０℃以上に加熱して脱水縮合反応させる工程を有する黒色化合物の製造方法。
Moreover, according to this invention, the manufacturing method of the black compound shown below is provided.
[ 3 ] A method for producing a black compound as described in [1] or [2 ] above, wherein the compound represented by the following general formula (2) is heated to 140 ° C. or higher to cause a dehydration condensation reaction. Compound production method.
さらに、本発明によれば、以下に示す着色剤が提供される。
［４］前記［１］又は［２］に記載の黒色化合物を含有する着色剤。
Furthermore, according to the present invention, the following colorant is provided.
[ 4 ] A colorant containing the black compound according to [1] or [2] .
本発明によれば、他の色材等と併用せずとも単独で黒色を呈することが可能な、無彩色度、黒色度、着色力、及び耐熱性に優れた黒色化合物及びその製造方法、並びにこの黒色化合物を用いた着色剤を提供することができる。 According to the present invention, a black compound excellent in achromaticity, blackness, coloring power, and heat resistance, capable of exhibiting black alone without being used in combination with other colorants, and a method for producing the same, and A colorant using this black compound can be provided.
＜黒色化合物＞
以下、本発明の実施の形態について説明するが、本発明は以下の実施の形態に限定されるものではない。本発明の黒色化合物は、下記一般式（１）で表される黒色化合物である。以下、その詳細について説明する。
Ｘ−（Ｙ）n−Ｚ ・・・（１）
（前記一般式（１）中、Ｘ、Ｙ、及びＺは、下記一般式（Ｘ）、（Ｙ）、及び（Ｚ）で表される部分構造Ｘ、Ｙ、及びＺをそれぞれ示し、ｎは、０〜５の整数を示す）
<Black compound>
Embodiments of the present invention will be described below, but the present invention is not limited to the following embodiments. The black compound of the present invention is a black compound represented by the following general formula (1). The details will be described below.
X- (Y) n -Z (1)
(In the general formula (1), X, Y, and Z represent partial structures X, Y, and Z represented by the following general formulas (X), (Y), and (Z), respectively, and n is Represents an integer of 0 to 5)
前記一般式（１）中のｎが０である場合、前記一般式（Ｘ）中の＊ｘ1は前記一般式（Ｚ）中の＊ｚ11又は＊ｚ12に結合し、＊ｘ2は＊ｚ2に結合している。
前記一般式（１）中のｎが１である場合、前記一般式（Ｘ）中の＊ｘ1は前記一般式（Ｙ）中の＊ｙ11又は＊ｙ12に結合し、＊ｘ2は＊ｙ2に結合している。また、前記一般式（Ｙ）中の＊ｙ1は前記一般式（Ｚ）中の＊ｚ11又は＊ｚ12に結合し、＊ｙ22は＊ｚ2に結合している。
前記一般式（１）中のｎが２〜５の整数である場合、前記一般式（Ｘ）中の＊ｘ1は前記一般式（Ｙ）中の＊ｙ11又は＊ｙ12に結合し、＊ｘ2は＊ｙ2に結合している。また、前記一般式（Ｙ）中の＊ｙ1は、隣接する部分構造Ｙを表す前記一般式（Ｙ）中の＊ｙ11又は＊ｙ12に結合し、＊ｙ22は＊ｙ2に結合している。但し、部分構造Ｘから最も離れた箇所に位置する部分構造Ｙについては、前記一般式（Ｙ）中の＊ｙ1は前記一般式（Ｚ）中の＊ｚ11又は＊ｚ12に結合し、＊ｙ22は＊ｚ2に結合している）
When n in the general formula (1) is 0, * x 1 in the general formula (X) is bonded to * z 11 or * z 12 in the general formula (Z), and * x 2 is It is attached to a * z 2.
When n in the general formula (1) is 1, * x 1 in the general formula (X) is bonded to * y 11 or * y 12 in the general formula (Y), and * x 2 is * are bound to y 2. Further, * y 1 in the general formula (Y) is bonded to * z 11 or * z 12 in the general formula (Z), and * y 22 is bonded to * z 2 .
When n in the general formula (1) is an integer of 2 to 5, * x 1 in the general formula (X) is bonded to * y 11 or * y 12 in the general formula (Y); * x 2 is attached to the * y 2. In addition, * y 1 in the general formula (Y) is bonded to * y 11 or * y 12 in the general formula (Y) representing the adjacent partial structure Y, and * y 22 is bonded to * y 2 . doing. However, for the partial structure Y located at the position farthest from the partial structure X, * y 1 in the general formula (Y) is bonded to * z 11 or * z 12 in the general formula (Z); * Y 22 is bonded to * z 2 )
１−アミノアントラキノンは、従来、顔料骨格として有用な化合物として知られている。具体的には、求核的なアミノ基と求電子的なカルボニル基の両方を分子内に有しており、その反応性の高さから様々な誘導体が合成されてきた。例えば、Ｎ−アシル化−１−アミノアントラキノンの挙動については数多く研究されており、Ｎ−アシル化−１−アミノアントラキノンを合成原料として用いることで、赤〜赤紫色の色相を有するアントラピリドン化合物が得られることが知られている。 1-aminoanthraquinone is conventionally known as a compound useful as a pigment skeleton. Specifically, it has both a nucleophilic amino group and an electrophilic carbonyl group in the molecule, and various derivatives have been synthesized due to its high reactivity. For example, many studies have been conducted on the behavior of N-acylated-1-aminoanthraquinone. By using N-acylated-1-aminoanthraquinone as a synthetic raw material, an anthrapyridone compound having a red to magenta hue can be obtained. It is known to be obtained.
本発明者らが下記一般式（２）で表される化合物を脱水縮合反応させたところ、赤〜赤紫色の色相を有する化合物を得ることはできず、黒色を呈する化合物が得られることが判明した。さらに検討した結果、本発明者らは、下記一般式（２）で表される１−アミノアントラキノン誘導体を脱水縮合反応させることで、無彩色度、黒色度、着色力、及び耐熱性に優れた、前記一般式（１）で表される黒色化合物が得られることを見出した。各種分析により、一般式（１）で表される黒色化合物は、原料として用いた一般式（２）で表される化合物が多量化することで広範囲の波長領域の光を吸収するようになり、黒色を呈することになったと推定される。 As a result of the dehydration condensation reaction of the compound represented by the following general formula (2) by the present inventors, it has been found that a compound having a red to magenta hue cannot be obtained and a compound exhibiting a black color is obtained. did. As a result of further investigation, the present inventors were excellent in achromaticity, blackness, coloring power, and heat resistance by subjecting the 1-aminoanthraquinone derivative represented by the following general formula (2) to a dehydration condensation reaction. The inventors have found that a black compound represented by the general formula (1) can be obtained. Through various analyses, the black compound represented by the general formula (1) absorbs light in a wide wavelength region by increasing the amount of the compound represented by the general formula (2) used as a raw material. It is presumed that the color became black.
一般式（１）中、ｎは１〜３の整数であることが好ましく、ｎは１であることがさらに好ましい。一般式（１）中のｎが上記の数値であると、黒色顔料としてより十分な特性を得ることができる。なお、ｎが０であると、黒の発色が不足する場合があるとともに、耐溶剤性や耐熱性などの顔料特性が低下することがある。一方、ｎが４以上であると、合成が困難となる場合がある。 In general formula (1), n is preferably an integer of 1 to 3, and n is more preferably 1. When n in the general formula (1) is the above numerical value, more sufficient characteristics as a black pigment can be obtained. When n is 0, black coloring may be insufficient, and pigment properties such as solvent resistance and heat resistance may deteriorate. On the other hand, when n is 4 or more, synthesis may be difficult.
本発明の黒色化合物の化学構造には、シス型（シス体）とトランス型（トランス体）の幾何異性体が存在すると考えられる。いずれの幾何異性体であっても、本発明の黒色化合物の概念に包含される。一般式（１）中のｎが０であり、一般式（Ｘ）及び（Ｚ）中のＲ１が水素原子である場合における、シス型とトランス型の例を以下に示す。 In the chemical structure of the black compound of the present invention, it is considered that there are geometric isomers of cis type (cis isomer) and trans type (trans isomer). Any geometric isomer is included in the concept of the black compound of the present invention. Examples of cis type and trans type in the case where n in the general formula (1) is 0 and R1 in the general formulas (X) and (Z) is a hydrogen atom are shown below.
本発明の黒色化合物の好適な具体例としては、下記式（１−１）〜（１−５）で表される化合物を挙げることができる。 Preferable specific examples of the black compound of the present invention include compounds represented by the following formulas (1-1) to (1-5).
本発明の黒色化合物は、以下に示すラクタム−ラクチム互変異性を示すと考えられる。いずれの互変異性体であっても、本発明の黒色化合物の概念に包含される。
＜黒色化合物の製造方法＞
次に、本発明の黒色化合物の製造方法について説明する。本発明の黒色化合物の製造方法は、下記一般式（２）で表される化合物を１４０℃以上に加熱して脱水縮合反応させる工程を有する。
<Method for producing black compound>
Next, the manufacturing method of the black compound of this invention is demonstrated. The manufacturing method of the black compound of this invention has the process of heating the compound represented by following General formula (2) to 140 degreeC or more, and carrying out a dehydration condensation reaction.
一般式（２）中のＲ1及びＲ2がいずれも水素原子である場合を例に挙げ、下記一般式（２）で表される化合物の脱水縮合の推定される反応機構を以下に示す。 The case where both R 1 and R 2 in the general formula (2) are hydrogen atoms is taken as an example, and the presumed reaction mechanism of the dehydration condensation of the compound represented by the following general formula (2) is shown below.
式（２）で表される化合物は、通常のＮ−アシル化−１−アミノアントラキノンと同様の挙動を示し、脱水縮合して、式（３）で表される中間体アントラピリドンを与える。さらに、式（３）で表される化合物は分子内アシル化反応を起こし、式（４）で表されるアザナフトアントロンを与える。式（４）で表される化合物はさらに多量化し、本発明の黒色化合物が得られると考えられる。 The compound represented by the formula (2) behaves in the same manner as a normal N-acylated-1-aminoanthraquinone, and is dehydrated to give an intermediate anthrapyridone represented by the formula (3). Furthermore, the compound represented by the formula (3) undergoes an intramolecular acylation reaction to give an azanaphthanthrone represented by the formula (4). It is considered that the compound represented by the formula (4) is further increased in quantity to obtain the black compound of the present invention.
脱水縮合反応は、適当な溶媒の存在下で実施することができる。溶媒としては、反応を短時間で簡潔に進行させることが可能であるために酸性溶媒が好ましい。酸性溶媒としては、酢酸、硫酸、ポリりん酸などを挙げることができる。酸性溶媒としてポリりん酸を用いると、副反応が生じにくくなるために好ましい。脱水縮合反応は１４０℃以上に加熱して実施する。加熱温度が１４０℃未満であると、脱水縮合そのものは進行するが、目的とする本発明の黒色化合物を得ることができない。なお、脱水縮合反応は、１４０〜２００℃に加熱して実施することが好ましい。 The dehydration condensation reaction can be carried out in the presence of a suitable solvent. As the solvent, an acidic solvent is preferable because the reaction can be easily proceeded in a short time. Examples of the acidic solvent include acetic acid, sulfuric acid, and polyphosphoric acid. It is preferable to use polyphosphoric acid as the acidic solvent because side reactions are unlikely to occur. The dehydration condensation reaction is carried out by heating to 140 ° C. or higher. If the heating temperature is less than 140 ° C., dehydration condensation itself proceeds, but the intended black compound of the present invention cannot be obtained. The dehydration condensation reaction is preferably carried out by heating to 140 to 200 ° C.
原料化合物として用いる一般式（２）で表される化合物は、例えば、１−アミノアントラキノンと、こはく酸又はこはく酸誘導体とを縮合反応させることで合成することができる。こはく酸誘導体としては、こはく酸一ナトリウム、こはく酸ジメチル、こはく酸ジエチル、こはく酸ジイソプロピル、こはく酸無水物などを挙げることができる。なかでも、こはく酸無水物を用いることが、縮合反応が円滑に進行するために好ましい。 The compound represented by the general formula (2) used as the raw material compound can be synthesized, for example, by subjecting 1-aminoanthraquinone and succinic acid or a succinic acid derivative to a condensation reaction. Examples of succinic acid derivatives include monosodium succinate, dimethyl succinate, diethyl succinate, diisopropyl succinate, and succinic anhydride. Of these, use of succinic anhydride is preferable because the condensation reaction proceeds smoothly.
＜着色剤＞
本発明の着色剤は、前述の黒色化合物を含有する。本発明の着色剤は、画像表示用、画像記録用、印刷インキ用、筆記用インキ用、プラスチック用、顔料捺染用、及び塗料用の着色剤などとして、広範な分野で用いることができる。また、本発明の着色剤は、インクジェット記録用インキ、電着記録液、電子写真方式用の現像剤などの画像記録剤用の材料としても有用である。これらの画像記録剤用の材料は、インクジェット記録方法、電着記録方式、電子写真方式などの画像記録方法にそれぞれ使用される。本発明の着色剤は、いずれの画像記録方法であっても高品位な画像を提供しうる画像記録剤用の材料として有用である。
<Colorant>
The colorant of the present invention contains the aforementioned black compound. The colorant of the present invention can be used in a wide range of fields such as for image display, image recording, printing ink, writing ink, plastic, pigment printing, and paint. The colorant of the present invention is also useful as a material for an image recording agent such as an ink for ink jet recording, an electrodeposition recording liquid, and a developer for electrophotography. These materials for the image recording agent are used for image recording methods such as an ink jet recording method, an electrodeposition recording method, and an electrophotographic method. The colorant of the present invention is useful as a material for an image recording agent that can provide a high-quality image by any image recording method.
本発明の着色剤は、通常、黒色化合物以外の成分として皮膜形成材料をさらに含有する。着色剤中の黒色化合物の量は、皮膜形成材料１００質量部に対して、５〜５００質量部であることが好ましく、５０〜２５０質量部であることがさらに好ましい。本発明の着色剤は、例えば、黒色化合物と、樹脂（（共）重合体）、オリゴマー、及びモノマーなどの皮膜形成材料とを混合することで調製することができる。 The colorant of the present invention usually further contains a film forming material as a component other than the black compound. The amount of the black compound in the colorant is preferably 5 to 500 parts by mass and more preferably 50 to 250 parts by mass with respect to 100 parts by mass of the film forming material. The colorant of the present invention can be prepared, for example, by mixing a black compound and a film forming material such as a resin ((co) polymer), an oligomer, and a monomer.
また、本発明の着色剤は、黒色化合物と、上記の皮膜形成材料とを含有する液とを混合することでも調製することができる。皮膜形成材料を含有する液としては、感光性の皮膜形成材料を含有する液や、非感光性の皮膜形成材料を含有する液などを挙げることができる。感光性の皮膜形成材料を含有する液の具体例としては、紫外線硬化性インキ、電子線硬化インキなどに用いられる感光性の皮膜形成材料を含有する液などを挙げることができる。また、非感光性の皮膜形成材料を含有する液の具体例としては、凸版インキ、平版インキ、グラビアインキ、スクリーンインキなどの印刷インキに使用するワニス；常温乾燥又は焼き付け塗料に使用するワニス；電着塗装に使用するワニス；熱転写リボンに使用するワニスなどを挙げることができる。 The colorant of the present invention can also be prepared by mixing a black compound and a liquid containing the above film forming material. Examples of the liquid containing the film forming material include a liquid containing a photosensitive film forming material and a liquid containing a non-photosensitive film forming material. Specific examples of the liquid containing the photosensitive film-forming material include liquid containing a photosensitive film-forming material used for ultraviolet curable ink, electron beam curable ink, and the like. Specific examples of liquids containing non-photosensitive film-forming materials include varnishes used for printing inks such as letterpress inks, lithographic inks, gravure inks and screen inks; varnishes used for room temperature drying or baking paints; Examples thereof include varnishes used for coating and varnishes used for thermal transfer ribbons.
感光性の皮膜形成材料の具体例としては、感光性環化ゴム系樹脂、感光性フェノール系樹脂、感光性ポリアクリレート系樹脂、感光性ポリアミド系樹脂、感光性ポリイミド系樹脂、不飽和ポリエステル系樹脂、ポリエステルアクリレート系樹脂、ポリエーテルアクリレート系樹脂、ポリオールアクリレート系樹脂などの感光性樹脂を挙げることができる。これらの感光性樹脂を含有する液には、反応性希釈剤として各種のモノマーを添加してもよい。 Specific examples of photosensitive film forming materials include photosensitive cyclized rubber resins, photosensitive phenol resins, photosensitive polyacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, and unsaturated polyester resins. And photosensitive resins such as polyester acrylate resins, polyether acrylate resins, and polyol acrylate resins. Various monomers may be added as reactive diluents to the liquid containing these photosensitive resins.
感光性樹脂を皮膜形成材料として含有する着色剤に、ベンゾインエーテル、ベンゾフェノンなどの光重合開始剤を添加し、従来公知の方法により練肉すれば、光硬化性の感光性顔料分散液とすることができる。また、上記の光重合開始剤に代えて熱重合開始剤を用いれば、熱硬化性顔料分散液とすることができる。 If a photopolymerization initiator such as benzoin ether or benzophenone is added to a colorant containing a photosensitive resin as a film-forming material and kneaded by a conventionally known method, a photocurable photosensitive pigment dispersion is obtained. Can do. Further, if a thermal polymerization initiator is used instead of the photopolymerization initiator, a thermosetting pigment dispersion can be obtained.
非硬化性の皮膜形成材料の具体例としては、スチレン−（メタ）アクリル酸エステル系共重合体、可溶性ポリアミド系樹脂、可溶性ポリイミド系樹脂、可溶性ポリアミドイミド系樹脂、可溶性ポリエステルイミド系樹脂、水溶性アミノポリエステル系樹脂、これらの水溶性塩、スチレン−マレイン酸エステル系共重合体の水溶性塩、（メタ）アクリル酸エステル−（メタ）アクリル酸系共重合体の水溶性塩などを挙げることができる。 Specific examples of non-curable film-forming materials include styrene- (meth) acrylic ester copolymers, soluble polyamide resins, soluble polyimide resins, soluble polyamideimide resins, soluble polyesterimide resins, and water-soluble materials. Examples include aminopolyester resins, water-soluble salts thereof, water-soluble salts of styrene-maleic acid ester copolymers, and water-soluble salts of (meth) acrylic acid ester- (meth) acrylic acid copolymers. it can.
以下、本発明を実施例に基づいて具体的に説明するが、本発明はこれらの実施例に限定されるものではない。なお、実施例、比較例中の「部」及び「％」は、特に断らない限り質量基準である。 EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example, this invention is not limited to these Examples. In the examples and comparative examples, “parts” and “%” are based on mass unless otherwise specified.
＜中間体の合成＞
酢酸２００部、１−アミノアントラキノン２２部、及びこはく酸無水物１１部を混合し、１１０℃で５時間加熱した。４０℃まで冷却した後、ろ過し、中性になるまで水で洗浄した。８０℃で乾燥して、下記式（２−１）で表される中間体（２−１）２６部を得た。得られた中間体（２−１）の1Ｈ−ＮＭＲの測定結果（ケミカルシフト）を以下に示す。また、赤外分光光度計（商品名「ＦＴ−７２０」、堀場製作所社製）を使用して測定した赤外吸収スペクトル（ＩＲチャート）を図１に示す。
1Ｈ−ＮＭＲ（ｄ−ＤＭＳＯ）：δ＝１２．１２（ｓ，１Ｈ，−ＣＯＯＨ），８．９４（ｍ，１Ｈ，ＮＨ），７．８７−８．２４（ｍ，７Ｈ，ＡｒＨ），２．７８（ｔ，２Ｈ，−ＣＨ2−），２．６２（ｔ，２Ｈ，−ＣＨ2）
<Synthesis of Intermediate>
200 parts of acetic acid, 22 parts of 1-aminoanthraquinone and 11 parts of succinic anhydride were mixed and heated at 110 ° C. for 5 hours. After cooling to 40 ° C., it was filtered and washed with water until neutral. It dried at 80 degreeC and obtained 26 parts of intermediate bodies (2-1) represented by a following formula (2-1). The measurement result (chemical shift) of 1 H-NMR of the obtained intermediate (2-1) is shown below. Further, FIG. 1 shows an infrared absorption spectrum (IR chart) measured using an infrared spectrophotometer (trade name “FT-720”, manufactured by HORIBA, Ltd.).
1 H-NMR (d-DMSO): δ = 12.12 (s, 1H, —COOH), 8.94 (m, 1H, NH), 7.87-8.24 (m, 7H, ArH), 2.78 (t, 2H, -CH 2 -), 2.62 (t, 2H, -CH 2)
＜黒色化合物等の合成＞
（実施例１）
ポリりん酸６０部及び中間体（２−１）５部を混合し、１７０℃で３時間加熱した。溶液が熱く、流動性があるうちに水６００部に注ぎ込み、３０分間撹拌した。析出物をろ過し、ろ液が中性になるまで水で洗浄した。析出物を８０℃で乾燥し、下記式（１−２）で表される黒色化合物（１−２）４部を得た。得られた化合物の赤外吸収スペクトル（ＩＲチャート）を図１に示す。図１に示すように、１７１０ｃｍ-1にあったアントラキノンカルボニルの吸収の消失が確認された。また、１６６０ｃｍ-1に新たに形成された架橋カルボニルの吸収が確認された。さらに、質量分析（ＭＡＬＤＩ）を行ったところ、以下の分子量に相当するピークが検出された。使用した原材料（中間体（２−１））及び質量分析の結果から、目的とする構造の顔料（黒色化合物（１−２））を得たことを確認した。
・分子量８３１／［Ｍ＋Ｎａ］＋
<Synthesis of black compounds>
Example 1
60 parts of polyphosphoric acid and 5 parts of intermediate (2-1) were mixed and heated at 170 ° C. for 3 hours. While the solution was hot and fluid, it was poured into 600 parts of water and stirred for 30 minutes. The precipitate was filtered and washed with water until the filtrate was neutral. The precipitate was dried at 80 ° C. to obtain 4 parts of a black compound (1-2) represented by the following formula (1-2). The infrared absorption spectrum (IR chart) of the obtained compound is shown in FIG. As shown in FIG. 1, the disappearance of absorption of anthraquinone carbonyl at 1710 cm −1 was confirmed. Moreover, absorption of the newly formed bridged carbonyl at 1660 cm −1 was confirmed. Furthermore, when mass spectrometry (MALDI) was performed, peaks corresponding to the following molecular weights were detected. From the raw material used (intermediate (2-1)) and the results of mass spectrometry, it was confirmed that the pigment (black compound (1-2)) having the target structure was obtained.
・ Molecular weight 831 / [M + Na] +
（比較例１）
ポリりん酸６０部及び中間体（２−１）５部の混合物を１２０℃で３時間加熱したこと以外は、前述の実施例１と同様にして、下記式（Ｂ）で表される暗茶色の化合物（Ｂ）４部を得た。得られた化合物（Ｂ）の1Ｈ−ＮＭＲの測定結果（ケミカルシフト）を以下に示す。また、赤外吸収スペクトル（ＩＲチャート）を図１に示す。
1Ｈ−ＮＭＲ（ｄ−ＤＭＳＯ）：δ＝７．７５−８．４０（ｍ，７Ｈ，Ａｒ−Ｈ），２．９５（ｓ，４Ｈ，−ＣＨ2−）
(Comparative Example 1)
A dark brown represented by the following formula (B) in the same manner as in Example 1 except that a mixture of 60 parts of polyphosphoric acid and 5 parts of intermediate (2-1) was heated at 120 ° C. for 3 hours. 4 parts of the compound (B) was obtained. The measurement result (chemical shift) of 1 H-NMR of the obtained compound (B) is shown below. An infrared absorption spectrum (IR chart) is shown in FIG.
1 H-NMR (d-DMSO): δ = 7.75-8.40 (m, 7H, Ar—H), 2.95 (s, 4H, —CH 2 —)
（比較例２）
特許文献１の［合成例２］に記載された方法にしたがって、下記式（Ｃ）で表される化合物（Ｃ）を合成した。
According to the method described in [Synthesis Example 2] of
（比較例３）
特許文献１の［比較合成例２］に記載された方法にしたがって、下記式（Ｄ）で表される化合物（Ｄ）を合成した。
A compound (D) represented by the following formula (D) was synthesized according to the method described in [Comparative Synthesis Example 2] of
＜濃色塗料の調製＞
実施例１及び比較例１〜３で得た各化合物（顔料）を以下に示す配合で混合した。ペイントコンディショナーを用いて９０分間分散させて濃色塗料を調製した。
・顔料 １．５部
・商品名「スーパーベッカミンＪ−８２０」（＊１） ８．５部
・商品名「フタルキッド１３３〜６０」（＊２） １７．０部
・キシレン／１−ブタノール（２／１質量比）混合溶剤 ５．０部
（＊１）ブチル化メラミン樹脂（大日本インキ化学工業社製）
（＊２）椰子油の短油性アルキド樹脂（日立化成社製）
<Preparation of dark paint>
Each compound (pigment) obtained in Example 1 and Comparative Examples 1 to 3 was mixed in the following composition. A dark paint was prepared by dispersing for 90 minutes using a paint conditioner.
-Pigment 1.5 parts-Trade name "Super Becamine J-820" (* 1) 8.5 parts-Trade name "Phthalkid 133-60" (* 2) 17.0 parts-Xylene / 1-butanol (2 / 1 mass ratio) Mixed solvent 5.0 parts (* 1) Butylated melamine resin (Dainippon Ink Chemical Co., Ltd.)
(* 2) Short oil alkyd resin of coconut oil (manufactured by Hitachi Chemical Co., Ltd.)
＜塗料試験＞
（１）色相、彩度、明度
アプリケーター（３ミル）を用いて濃色塗料をアート紙上に展色し、１４０℃で３０分間焼き付けて塗膜を形成した。塗膜を測色計で計測（Ｌ*Ｃ*ｈ*表色系）し、以下に示す基準にしたがって無彩色度及び黒色度を評価した。結果を表１に示す。
［無彩色度］
○：無彩色度が非常に高い（Ｃ*＜２）
△：無彩色度が高い（２≦Ｃ*＜５）
×：無彩色度が低い（Ｃ*≧５）
［黒色度］
○：黒色度が非常に高い（Ｌ*＜３）
△：黒色度が高い（３≦Ｌ*＜５）
×：黒色度が低い（Ｌ*≧５）
<Paint test>
(1) Hue, Saturation, Lightness Using an applicator (3 mil), a dark paint was developed on art paper and baked at 140 ° C. for 30 minutes to form a coating film. The coating film was measured with a colorimeter (L * C * h * color system), and the achromaticity and blackness were evaluated according to the following criteria. The results are shown in Table 1.
[Achromaticity]
○: Achromaticity is very high (C * <2)
Δ: High achromaticity (2 ≦ C * <5)
×: Low achromaticity (C * ≧ 5)
[Blackness]
○: Blackness is very high (L * <3)
Δ: High blackness (3 ≦ L * <5)
X: Low blackness (L * ≧ 5)
（２）着色力
チタンホワイト（酸化チタン）を含む白色塗料を用いて、顔料：チタンホワイト＝１：２０（質量比）となるように濃色塗料を希釈して淡色塗料を調製した。アプリケーター（６ミル）を用いて淡色塗料をアート紙上に展色し、１４０℃で３０分間焼き付けて塗膜を形成した。塗料を肉眼で観察し、以下に示す基準にしたがって着色力を評価した。結果を表１に示す。
○：着色力良好
△：着色力あり
×：着色力なし
(2) Coloring power Using a white paint containing titanium white (titanium oxide), a dark paint was prepared by diluting the dark paint so that pigment: titanium white = 1: 20 (mass ratio). A light color paint was spread on art paper using an applicator (6 mil) and baked at 140 ° C. for 30 minutes to form a coating film. The paint was observed with the naked eye, and the coloring power was evaluated according to the following criteria. The results are shown in Table 1.
○: Good coloring power △: High coloring power ×: No coloring power
＜耐熱性試験＞
（３）耐熱性
製造した各顔料について示差熱重量分析（ＴＧ−ＤＴＡ）を行い、以下に示す基準にしたがって耐熱性を評価した。結果を表１に示す。
○：耐熱性良好（３５０℃において０％以上１０％未満の質量減少）
△：耐熱性あり（３５０℃において１０％以上２０％未満の質量減少）
×：耐熱性なし（３５０℃において２０％以上の質量減少）
<Heat resistance test>
(3) Heat resistance A differential thermogravimetric analysis (TG-DTA) was performed on each manufactured pigment, and the heat resistance was evaluated according to the following criteria. The results are shown in Table 1.
○: Good heat resistance (mass decrease of 0% or more and less than 10% at 350 ° C)
Δ: heat resistance (mass decrease of 10% or more but less than 20% at 350 ° C)
X: No heat resistance (mass loss of 20% or more at 350 ° C.)
本発明の黒色化合物は、印刷インキ（オフセットインキ、グラビアインキなど）、各種塗料、プラスチック、顔料捺染剤、電子写真用乾式・湿式トナー、インクジェット記録用インキ、熱転写記録用インキ、カラーフィルター用レジスト、筆記具用インキなどに使用される顔料として有用である。 The black compound of the present invention includes printing ink (offset ink, gravure ink, etc.), various paints, plastic, pigment printing agent, electrophotographic dry / wet toner, ink jet recording ink, thermal transfer recording ink, color filter resist, It is useful as a pigment used in ink for writing instruments.
Claims (4)
Ｘ−（Ｙ）n−Ｚ ・・・（１）
（前記一般式（１）中、Ｘ、Ｙ、及びＺは、下記一般式（Ｘ）、（Ｙ）、及び（Ｚ）で表される部分構造Ｘ、Ｙ、及びＺをそれぞれ示し、ｎは、１を示す）
前記一般式（Ｘ）中の＊ｘ1は前記一般式（Ｙ）中の＊ｙ11 に結合し、＊ｘ2は＊ｙ2に結合している。また、前記一般式（Ｙ）中の＊ｙ1は前記一般式（Ｚ）中の＊ｚ11 に結合し、＊ｙ22は＊ｚ2に結合している） A black compound represented by the following general formula (1).
X- (Y) n -Z (1)
(In the general formula (1), X, Y, and Z represent partial structures X, Y, and Z represented by the following general formulas (X), (Y), and (Z), respectively, and n is , Indicating 1 )
Before SL * x 1 in the general formula (X) is bonded to * y 1 1 in the general formula (Y), * x 2 is attached to the * y 2. Also, * y 1 in the general formula (Y) is coupled to * z 1 1 in the general formula (Z), * y 22 is that bonded to * z 2)
下記一般式（２）で表される化合物を１４０℃以上に加熱して脱水縮合反応させる工程を有する黒色化合物の製造方法。
The manufacturing method of the black compound which has the process of heating the compound represented by following General formula (2) to 140 degreeC or more, and carrying out a dehydration condensation reaction.
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| CN110526826A (en) * | 2019-08-22 | 2019-12-03 | 中盐金坛盐化有限责任公司 | Synthetic method, derivative and the battery system of anthraquinone derivative containing carboxyl |
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| CN110526826A (en) * | 2019-08-22 | 2019-12-03 | 中盐金坛盐化有限责任公司 | Synthetic method, derivative and the battery system of anthraquinone derivative containing carboxyl |
| WO2021032156A1 (en) * | 2019-08-22 | 2021-02-25 | 中盐金坛盐化有限责任公司 | Method for synthesizing carboxy-containing anthraquinone derivative, obtained derivative, and battery system comprising same |
| CN110526826B (en) * | 2019-08-22 | 2022-12-02 | 中盐金坛盐化有限责任公司 | Method for synthesizing anthraquinone derivative containing carboxyl, derivative and battery system |
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